Rub the rim of an old-fashioned glass with the lemon and dip in the powdered sugar. Stir or briefly shake the brandy, bitters and curacao over cracked ice. Pour into the prepared glass, garnish with the lemon and serve.

Recipes seem to be divided as to whether you strain out the ice and, as in the linked video, the sugared glass rim can be dispensed with. However, a much classier version is given in the 1930 Savoy Cocktail Book This addition, too, is variable. Some recipes call for dry white wine in lieu of champagne, notes Hubie Greenwald, owner of The Motel Bar in River North.

Why brandy? I don’t know that either, but the drink certainly originated before Prohibition and bathtub bootlegging, which explains why it isn’t the gin-based libation one might assume would be linked to our fair city.

“It’s kind of an odd combination of sprits,” says Greenwald, who is not a fan. “It’s sweet.”

“Chicago has been a town for whiskey and scotch … and beer,” says Adam Seger, mixologist at Nacional 27 in River North. “It’s an odd fit, and that may be why it hasn’t caught on here, despite all the interest in retro cocktails.

“I’m wondering whether it was a drink out of Milwaukee or somewhere and they just called it a ‘Chicago cocktail,'” Seger speculates. Wisconsin, which has the highest per capita consumption of brandy in the country, much of it going into brandy old fashioned sweets, certainly makes more sense as the birthplace of another syrupy, brandy-based cocktail.

“It seems to me the etymology of a lot of these cocktails is kind of convoluted,” agrees Greenwald.

Take for example, the Southside cocktail, a tall, cool libation of gin, lemon juice, sugar, mint and soda; many people think it’s named for South Side Chicago, but it’s much more likely it was invented at the Southside Sportsmen’s Club in New York.

Like the Southside, the Chicago cocktail turns up in all kinds of recipe collections, but there’s little evidence it was ever popular here. John Drury gives the recipe in his 1931 “Dining in Chicago,” but that doesn’t get us anywhere since he was too savvy to name any local establishments actually serving it during Prohibition, just saying that one “Robert, of the American Bar at Nice, and formerly of the Embassy Club, London, vouches for the Chicago Cocktail and you’ll agree that his vouching is above question.”

Some drink manuals also list the equally venerable Chicago fizz, an even more unlikely highball made with rum, port, lemon, powdered sugar, egg white and seltzer. I’ve never seen that on a menu and I bet you’d get shrugs if you tried to order it anywhere — not that I’d want to.

At Nacional 27, Seger has come up with his own version of a local cocktail, which he calls the Chicagoan: It’s Irish whiskey and sour mix topped with Goose Island Beer’s312 Urban Wheat and garnished with a sport pepper.

Brandy cocktails like the sidecar used to be fairly popular in the old days, so I don’t find it very surprising. I find brandy to be a pretty good base for a sweet cocktail, more flavor than vodka obviously and it doesn’t clash like harsh whiskey.